US2024051981A1PendingUtilityA1
Composition, light-emitting device, electronic apparatus including the light-emitting device, and organometallic compound
Est. expiryJul 20, 2042(~16 yrs left)· nominal 20-yr term from priority
C07F 15/0086H10K 50/12H10K 85/346H10K 85/654H10K 85/6572C07B 2200/05H10K 2101/30C09K 11/06C09K 2211/185
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Claims
Abstract
An organic light-emitting device includes a first electrode, a second electrode facing the first electrode, and an interlayer between the first electrode and the second electrode and including an organometallic compound represented by Formula 1. In addition, an electronic apparatus including the light-emitting device, a composition including the organometallic compound represented by Formula 1, and an organometallic compound represented by Formula 1 are also provided.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A composition comprising:
an organometallic compound represented by Formula 1; and a second compound comprising at least one π electron-deficient nitrogen-containing C 1 -C 60 heterocyclic group, a third compound comprising a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, wherein each of the organometallic compound, the second compound, the third compound, and the fourth compound are different from each other:
wherein, in Formula 1,
M is platinum (Pt), palladium (Pd), gold (Au), nickel (N 1 ), silver (Ag), or copper (Cu),
X 1 to X 4 are each independently C or N,
i) a bond between X 1 and M is a coordinate bond, ii) one selected from among a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond, and the other two are each a covalent bond,
ring CY 1 and ring CY 2 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
ring CY 3 is a C 2 -C 8 monocyclic group or a C 4 -C 20 polycyclic group in which two or three C 2 -C 8 monocyclic groups are condensed together,
X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, X 43 is C(R 43 ) or N, and X 44 is C(R 44 ) or N,
each of ring CY 11 , ring CY 12 , and ring CY 13 is a C 2 -C 8 monocyclic group,
X 51 is a single bond, *—N(Z 51a )—*′, *—B(Z 51a )—*′, *—P(Z 51a )—*′, *—C(Z 51a )(Z 51b )—*′, *—Si(Z 51a )(Z 51b )—*′, *—Ge(Z 51a )(Z 51b )—*, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(Z 51a )=*′, *═C(Z 51a )—*′, *—C(Z 51a )═C(Z 51b )—*′, *—C(═S)—*′, or *—C≡C—*′,
X 52 is a single bond, *—N(Z 52a )—*′, *—B(Z 52a )—*′, *—P(Z 52a )—*′, *—C(Z 52a )(Z 52b )—*′, *—Si(Z 52a )(Z 52b )—*′, *—Ge(Z 52a )(Z 52b )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(Z 52a )=*′, *═C(Z 52a )—*′, *—C(Z 52a )═C(Z 52b )—*′, *—C(═S)—*′, or *—C≡C—*′,
R 1 to R 3 , R 41 , R 42 , R 44 , Z 51a , Z 51b , Z 52a , Z 52b , and T 1 to T 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group that is unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group that is unsubstituted or substituted with at least one R 10a , a C 7 -C 60 aryl alkyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 heteroaryl alkyl group that is unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
R 43 is hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group that is unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
a1, a2, a3, c2, and c3 are each independently an integer from 0 to 10,
c1 is an integer from 0 to 5,
a group represented by
and a group represented by
are different from each other,
i) two or more of a1 R 1 (s) when a1 is two or more, ii) two or more of a2 R 2 (s) when a2 is two or more, iii) two or more of R 41 to R 44 , and iv) two or more of R 1 to R 3 , R 41 to R 44 , Z 51a , Z 51b , Z 52a , and Z 52b are each optionally bonded together to form a C 3 -C 20 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more of a3 R 3 (s) when a3 is two or more are not linked together,
two or more of T 1 to T 3 are not linked together,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, a C 2 -C 60 heteroaryl alkyl group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, or a C 2 -C 60 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, a C 2 -C 60 heteroaryl alkyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —CI; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof,
wherein, in Formula 3,
ring CY 71 and ring CY 72 are each independently a π electron-rich C 3 -C 60 cyclic group or a pyridine group,
X 71 is a single bond, or a linking group comprising O, S, N, B, C, Si, or any combination thereof, and
* indicates a binding site to an atom included in a remainder of the third compound, other than Formula 3.
2 . A light-emitting device comprising:
a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and comprising an emission layer; and an organometallic compound represented by Formula 1:
wherein, in Formula 1,
M is platinum (Pt), palladium (Pd), gold (Au), nickel (N 1 ), silver (Ag), or copper (Cu),
X 1 to X 4 are each independently C or N,
i) a bond between X 1 and M is a coordinate bond, ii) one selected from among a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond, and the other two are each a covalent bond,
ring CY 1 and ring CY 2 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
ring CY 3 is a C 2 -C 8 monocyclic group or a C 4 -C 20 polycyclic group in which two or three C 2 -C 8 monocyclic groups are condensed together,
X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, X 43 is C(R 43 ) or N, and X 44 is C(R 44 ) or N, each of ring CY 11 , ring CY 12 , and ring CY 13 is a C 2 -C 8 monocyclic group,
X 51 is a single bond, *—N(Z 51a )—*′, *—B(Z 51a )—*, *—P(Z 51a )—*′, *—C(Z 51a )(Z 51b )—*′, *—Si(Z 51a )(Z 51b )—*′, *—Ge(Z 51a )(Z 51b )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(O)—*″, *—S(═O) 2 —*′, *—C(Z 51a )=*′, *═C(Z 51a )—*′, *—C(Z 51a )═C(Z 51b )—*′, *—C(═S)—*′, or *—C≡C—*′,
X 52 is a single bond, *—N(Z 52a )—*′, *—B(Z 52a )—*′, *—P(Z 52a )—*′, *—C(Z 52a )(Z 52b )—*′, *—Si(Z 52a )(Z 52b )—*′, *—Ge(Z 52a )(Z 52b )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(Z 52a )=*′, *═C(Z 52a )—*′, *—C(Z 52a )═C(Z 52b )—*′, *—C(═S)—*′, or *—C≡C—*′,
R 1 to R 3 , R 41 , R 42 , R 44 , Z 51a , Z 51b , Z 52a , Z 52b , and T 1 to T 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group that is unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group that is unsubstituted or substituted with at least one R 10a , a C 7 -C 60 aryl alkyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 heteroaryl alkyl group that is unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
R 43 is hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group that is unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
a1, a2, a3, c2, and c3 are each independently an integer from 0 to 10,
c1 is an integer from 0 to 5,
a group represented by
and a group represented by
are different from each other,
i) two or more of a1 R 1 (s) when a1 is two or more, ii) two or more of a2 R 2 (s) when a2 is two or more, iii) two or more of R 41 to R 44 , and iv) two or more of R 1 to R 3 , R 41 to R 44 , Z 51a , Z 51b , Z 52a , and Z 52b are each optionally bonded together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more of a3 R 3 (s) when a3 is two or more are not linked together,
two or more of T 1 to T 3 are not linked together,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, a C 2 -C 60 heteroaryl alkyl group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, or a C 2 -C 60 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, a C 2 -C 60 heteroaryl alkyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
3 . The light-emitting device of claim 2 , further comprising a second compound comprising at least one π electron-deficient nitrogen-containing C 1 -C 60 heterocyclic group, a third compound comprising a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof,
wherein the organometallic compound, the second compound, the third compound, and the fourth compound are different from each other:
wherein, in Formula 3,
ring CY 71 and ring CY 72 are each independently a π electron-rich C 3 -C 60 cyclic group or a pyridine group,
X 71 is a single bond, or a linking group comprising O, S, N, B, C, Si, or any combination thereof, and
* indicates a binding site to an atom included in a remainder of the third compound, other than Formula 3.
4 . The light-emitting device of claim 3 , wherein the second compound comprises a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof, and
the fourth compound comprises at least one cyclic group comprising both boron (B) and nitrogen (N) as ring-forming atoms.
5 . The light-emitting device of claim 3 , wherein the emission layer comprises:
i) the organometallic compound; and ii) the second compound, the third compound, the fourth compound, or any combination thereof, and the emission layer is to emit blue light.
6 . The light-emitting device of claim 3 , further comprising the second compound and the third compound,
wherein at least one selected from among the second compound and the third compound comprises at least one deuterium, at least one silicon, or a combination thereof.
7 . An electronic device comprising the light-emitting device of claim 2 .
8 . The electronic device of claim 7 , further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
9 . An electronic apparatus comprising the light-emitting device of claim 2 .
10 . The electronic apparatus of claim 9 , wherein the electronic apparatus is at least one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and/or light for signal, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.
11 . An organometallic compound represented by Formula 1:
wherein, in Formula 1,
M is platinum (Pt), palladium (Pd), gold (Au), nickel (N 1 ), silver (Ag), or copper (Cu),
X 1 to X 4 are each independently C or N,
i) a bond between X 1 and M is a coordinate bond, ii) one selected from among a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond, and the other two are each a covalent bond,
ring CY 1 and ring CY 2 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
ring CY 3 is a C 2 -C 8 monocyclic group or a C 4 -C 20 polycyclic group in which two or three C 2 -C 8 monocyclic groups are condensed together,
X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, X 43 is C(R 43 ) or N, and X 44 is C(R 44 ) or N, each of ring CY 11 , ring CY 12 , and ring CY 13 is a C 2 -C 8 monocyclic group,
X 51 is a single bond, *—N(Z 51a )—*′, *—B(Z 51a )—*′, *—P(Z 51a )—*′, *—C(Z 51a )(Z 51b )—*′, *—Si(Z 51a )(Z 51b )—*′, *—Ge(Z 51a )(Z 51b )—*, *—S—*, *—Se—*, *—O—*, *—C(═O)—*, *—S(═O)—*′ *—S(═O) 2 —*′, *—C(Z 51a )=*′, *═C(Z 51a )-*′, *—C(Z 51a )═C(Z 51b )—*′, *—C(═S)—*′, or *—C≡C—*′,
X 52 is a single bond, *—N(Z 52a )—*, *—B(Z 52a )—*′, *—P(Z 52a )—*′, *—C(Z 52a )(Z 52b )—*′, *—Si(Z 52a )(Z 52b )—*′, *—Ge(Z 52a )(Z 52b )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(Z 52a )=*′, *═C(Z 52a )—*′, *—C(Z 52a )═C(Z 52b )—*′, *—C(═S)—*′, or *—C≡C—*′,
R 1 to R 3 , R 41 , R 42 , R 44 , Z 51a , Z 51b , Z 52a , Z 52b , and T 1 to T 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group that is unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group that is unsubstituted or substituted with at least one R 10a , a C 7 -C 60 aryl alkyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 heteroaryl alkyl group that is unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
R 43 is hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group that is unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
a1, a2, a3, c2, and c3 are each independently an integer from 0 to 10,
c1 is an integer from 0 to 5,
a group represented by
and a group represented by
are different from each other,
i) two or more of a1 R 1 (s) when a1 is two or more, ii) two or more of a2 R 2 (s) when a2 is two or more, iii) two or more of R 41 to R 44 , and iv) two or more of R 1 to R 3 , R 41 to R 44 , Z 51a , Z 51b , Z 52a , and Z 52b are each optionally bonded together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more of a3 R 3 (s) when a3 is two or more are not linked together,
two or more of T 1 to T 3 are not linked together,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, a C 2 -C 60 heteroaryl alkyl group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, or a C 2 -C 60 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, a C 2 -C 60 heteroaryl alkyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
12 . The organometallic compound of claim 11 , wherein X 1 is C, and
ring CY 1 is an imidazole group, a triazole group, a benzimidazole group, a naphthoimidazole group, or an imidazopyridine group.
13 . The organometallic compound of claim 11 , wherein ring CY 11 , ring CY 12 , and ring CY 13 are identical to each other.
14 . The organometallic compound of claim 11 , wherein R 1 to R 3 , R 41 , R 42 , R 44 , Z 51a , Z 51b , Z 52a , Z 52b , and T 1 to T 3 are each independently:
hydrogen, deuterium, —F, or a cyano group; a C 1 -C 20 alkyl group that is unsubstituted or substituted with deuterium, —F, a cyano group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C 1 -C 20 alkyl)biphenyl group, or any combination thereof; or a C 3 -C 1 cycloalkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl) phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C 1 -C 20 alkyl)biphenyl group, or any combination thereof, and R 43 is: hydrogen, deuterium, —F, or a cyano group; or a C 1 -C 20 alkyl group that is unsubstituted or substituted with deuterium, —F, a cyano group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C 1 -C 20 alkyl)biphenyl group, or any combination thereof.
15 . The organometallic compound of claim 11 , wherein the organometallic compound comprises at least one deuterium.
16 . The organometallic compound of claim 11 , wherein a group represented by
in Formula 1 is a group represented by Formula AS1:
and
wherein, in Formula AS1,
ring CY 12 , ring CY 13 , T 2 , T 3 , c2, and c3 are each defined as in Formula 1,
Y 1 is C(T 11 ) or N, Y2 is C(T 12 ) or N, and Y 3 is C(T 13 ) or N,
T 11 to T 13 are each the same as defined with respect to T 1 in Formula 1,
* is a binding site to ring CY 1 in Formula 1.
17 . The organometallic compound of claim 11 , wherein i) c2 and c3 are different from each other, or
ii) each of c2 and c3 is not 0, and one of c2 T 2 and one of c3 T 3 are different from each other.
18 . The organometallic compound of claim 11 , wherein in Formula 1, a group represented by
is a group represented by Formula AS2,
a group represented by
is a group represented by Formula AS3, and
i) Condition C 1 is satisfied, or ii) at least one selected from among Condition C 2 to Condition C 6 is satisfied:
and
wherein T 21 to T 25 in Formula AS2 are each the same as defined with respect to T 2 in Formula 1, and * indicates a binding site to ring CY 11 , and
T 31 to T 35 in Formula AS3 are each the same as defined with respect to T 3 in Formula 1, and * indicates a binding site to ring CY 11 :
Condition C 1
a number of groups that are not hydrogen among T 21 to T 25 in Formula AS2 and a number of groups that are not hydrogen among T 31 to T 35 in Formula AS3 are different from each other;
Condition C 2
T 21 and T 31 are different from each other;
Condition C 3
T 22 and T 32 are different from each other;
Condition C 4
T 23 and T 33 are different from each other;
Condition C 5
T 24 and T 34 are different from each other; and
Condition C 6
T 25 and T 35 are different from each other.
19 . The organometallic compound of claim 18 , wherein each of T 21 to T 25 in Formula AS2 is not hydrogen, and
Formula AS3 satisfies Condition D1 or Condition D2: Condition D1 each of T 31 , T 33 , and T 35 is hydrogen, and each of T 32 and T 34 is not hydrogen; or Condition D2 each of T 31 , T 33 , T 34 , and T 35 is hydrogen, and T 32 is not hydrogen.
20 . The organometallic compound of claim 11 , wherein the organometallic compound is represented by Formula 1-1 or 1-2:
and
wherein, in Formulae 1-1 and 1-2,
M, X 1 to X 4 , X 41 to X 44 , and X 51 are each defined as in Formula 1,
X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, and X 14 is C(R 14 ) or N,
R 11 to R 14 are each the same as defined with respect to R 1 in Formula 1, and two or more of R 11 to R 14 are optionally bonded together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
X 21 is C(R 21 ) or N, X 22 is C(R 22 ) or N, and X 23 is C(R 23 ) or N,
R 21 to R 23 are each the same as defined with respect to R 2 in Formula 1, and two or more of R 21 to R 23 are optionally bonded together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
X 31 is C(R 31 ) or N, X 32 is C(R 32 ) or N, X 33 is C(R 33 ) or N, X 34 is C(R 34 ) or N, X 35 is C(R 35 ) or N, and X 36 is C(R 36 ) or N,
R 31 to R 36 are each the same as defined with respect to R 3 in Formula 1, and two or more of R 31 to R 36 are not linked together,
Y 1 is C(T 11 ) or N, Y 2 is C(T 12 ) or N, and Y 3 is C(T 13 ) or N,
T 11 to T 13 are each the same as defined with respect to T 1 in Formula 1,
T 21 to T 25 are each the same as defined with respect to T 2 in Formula 1,
T 31 to T 35 are each the same as defined with respect to T 3 in Formula 1,
two or more of T 11 to T 13 , T 21 to T 25 , and T 31 to T 35 are not linked together, and a group represented by
and a group represented by
are different from each other.Join the waitlist — get patent alerts
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